JP5460584B2 - ジニトロピラゾール誘導体、その製造方法、及び、それを含む活性化合物 - Google Patents
ジニトロピラゾール誘導体、その製造方法、及び、それを含む活性化合物 Download PDFInfo
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- JP5460584B2 JP5460584B2 JP2010511742A JP2010511742A JP5460584B2 JP 5460584 B2 JP5460584 B2 JP 5460584B2 JP 2010511742 A JP2010511742 A JP 2010511742A JP 2010511742 A JP2010511742 A JP 2010511742A JP 5460584 B2 JP5460584 B2 JP 5460584B2
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- Prior art keywords
- compound
- dinitropyrazole
- formula
- salt
- trinitropyrazole
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 93
- 238000000034 method Methods 0.000 title claims description 22
- UKZXCZWGGXVKNN-UHFFFAOYSA-N 3,5-dinitro-1h-pyrazole Chemical class [O-][N+](=O)C=1C=C([N+]([O-])=O)NN=1 UKZXCZWGGXVKNN-UHFFFAOYSA-N 0.000 title claims description 18
- 150000003839 salts Chemical class 0.000 claims description 39
- YLTPBDJQPIRWTQ-UHFFFAOYSA-N 3,4,5-trinitro-1h-pyrazole Chemical compound [O-][N+](=O)C1=NNC([N+]([O-])=O)=C1[N+]([O-])=O YLTPBDJQPIRWTQ-UHFFFAOYSA-N 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 27
- 239000002360 explosive Substances 0.000 claims description 24
- UBOMOJSHQSDQOE-UHFFFAOYSA-N 1,3,4-trinitropyrazole Chemical compound [O-][N+](=O)C1=CN([N+]([O-])=O)N=C1[N+]([O-])=O UBOMOJSHQSDQOE-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 238000006396 nitration reaction Methods 0.000 claims description 11
- 239000011230 binding agent Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 9
- ZDCGXVZZNAVVFJ-UHFFFAOYSA-N 3,5-dinitro-1h-pyrazol-4-amine Chemical compound NC=1C([N+]([O-])=O)=NNC=1[N+]([O-])=O ZDCGXVZZNAVVFJ-UHFFFAOYSA-N 0.000 claims description 8
- JDAQETOZCRMAJU-UHFFFAOYSA-N 4,5-dinitro-1,2-dihydropyrazol-3-one Chemical compound OC=1NN=C([N+]([O-])=O)C=1[N+]([O-])=O JDAQETOZCRMAJU-UHFFFAOYSA-N 0.000 claims description 6
- MHHCWYNIYJZBIC-UHFFFAOYSA-N 3,5-dinitro-1h-pyrazol-4-ol Chemical compound OC=1C([N+]([O-])=O)=NNC=1[N+]([O-])=O MHHCWYNIYJZBIC-UHFFFAOYSA-N 0.000 claims description 5
- VXMCBBMNFIAYQD-UHFFFAOYSA-N 4,5-dinitro-1h-pyrazole Chemical compound [O-][N+](=O)C=1C=NNC=1[N+]([O-])=O VXMCBBMNFIAYQD-UHFFFAOYSA-N 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- MZRUFMBFIKGOAL-UHFFFAOYSA-N 5-nitro-1h-pyrazole Chemical group [O-][N+](=O)C1=CC=NN1 MZRUFMBFIKGOAL-UHFFFAOYSA-N 0.000 claims description 4
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentoxide Inorganic materials [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 claims description 4
- 230000000802 nitrating effect Effects 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- YNGRGHODNDCZCC-UHFFFAOYSA-N nitro hydrogen sulfate Chemical compound OS(=O)(=O)O[N+]([O-])=O YNGRGHODNDCZCC-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- HAMNKKUPIHEESI-UHFFFAOYSA-O carbamohydrazonoylazanium Chemical compound NC(N)=N[NH3+] HAMNKKUPIHEESI-UHFFFAOYSA-O 0.000 claims 1
- FQQQSNAVVZSYMB-UHFFFAOYSA-O diamino(diaminomethylidene)azanium Chemical compound N[NH+](N)C(N)=N FQQQSNAVVZSYMB-UHFFFAOYSA-O 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims 1
- 239000000047 product Substances 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 230000035945 sensitivity Effects 0.000 description 21
- UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 description 15
- 239000000028 HMX Substances 0.000 description 13
- ZVRADRYJGLEDDP-UHFFFAOYSA-N 3,4-dinitro-1h-pyrazol-5-amine Chemical compound NC=1NN=C([N+]([O-])=O)C=1[N+]([O-])=O ZVRADRYJGLEDDP-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- -1 Alkali metal cations Chemical class 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000003380 propellant Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000009286 beneficial effect Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- POSJHBBNJCTDEZ-UHFFFAOYSA-N 5-azido-3,4-dinitro-1h-pyrazole Chemical compound [O-][N+](=O)C1=NNC(N=[N+]=[N-])=C1[N+]([O-])=O POSJHBBNJCTDEZ-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- FDIMEMAIDTUNPZ-UHFFFAOYSA-N n,n-difluoro-3,5-dinitro-1h-pyrazol-4-amine Chemical compound [O-][N+](=O)C1=NNC([N+]([O-])=O)=C1N(F)F FDIMEMAIDTUNPZ-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 238000003682 fluorination reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- BEGIHXRNDMXESM-UHFFFAOYSA-N n,n-difluoro-4,5-dinitro-1h-pyrazol-3-amine Chemical compound [O-][N+](=O)C1=NNC(N(F)F)=C1[N+]([O-])=O BEGIHXRNDMXESM-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 229910052573 porcelain Inorganic materials 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- NDYLCHGXSQOGMS-UHFFFAOYSA-N CL-20 Chemical compound [O-][N+](=O)N1C2N([N+]([O-])=O)C3N([N+](=O)[O-])C2N([N+]([O-])=O)C2N([N+]([O-])=O)C3N([N+]([O-])=O)C21 NDYLCHGXSQOGMS-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004455 differential thermal analysis Methods 0.000 description 2
- OMBRFUXPXNIUCZ-UHFFFAOYSA-N dioxidonitrogen(1+) Chemical compound O=[N+]=O OMBRFUXPXNIUCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010892 electric spark Methods 0.000 description 2
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- PPXCEVIBCCTNJB-UHFFFAOYSA-N n-(3,4-dinitro-1h-pyrazol-5-yl)hydroxylamine Chemical compound ONC=1NN=C([N+]([O-])=O)C=1[N+]([O-])=O PPXCEVIBCCTNJB-UHFFFAOYSA-N 0.000 description 2
- IVFBLWCMWWCOJF-UHFFFAOYSA-N n-(3,5-dinitro-1h-pyrazol-4-yl)hydroxylamine Chemical compound ONC=1C([N+]([O-])=O)=NNC=1[N+]([O-])=O IVFBLWCMWWCOJF-UHFFFAOYSA-N 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- JDFUJAMTCCQARF-UHFFFAOYSA-N tatb Chemical compound NC1=C([N+]([O-])=O)C(N)=C([N+]([O-])=O)C(N)=C1[N+]([O-])=O JDFUJAMTCCQARF-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- XFSZIRDUESXNJM-UHFFFAOYSA-N (3,4-dinitro-1h-pyrazol-5-yl)hydrazine Chemical compound NNC=1NN=C([N+]([O-])=O)C=1[N+]([O-])=O XFSZIRDUESXNJM-UHFFFAOYSA-N 0.000 description 1
- CZFFPQCVJBGSRA-UHFFFAOYSA-N (3,5-dinitro-1h-pyrazol-4-yl)hydrazine Chemical compound NNC=1C([N+]([O-])=O)=NNC=1[N+]([O-])=O CZFFPQCVJBGSRA-UHFFFAOYSA-N 0.000 description 1
- POCJOGNVFHPZNS-ZJUUUORDSA-N (6S,7R)-2-azaspiro[5.5]undecan-7-ol Chemical compound O[C@@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-ZJUUUORDSA-N 0.000 description 1
- RSXKSXDNAQPZQD-UHFFFAOYSA-N 1,4-dinitropyrazole Chemical class [O-][N+](=O)C=1C=NN([N+]([O-])=O)C=1 RSXKSXDNAQPZQD-UHFFFAOYSA-N 0.000 description 1
- CMDORWSHEWRPMO-UHFFFAOYSA-N 2,4,5-trinitrocyclohexa-1,3-diene-1,3,5-triamine Chemical compound NC1=C([N+]([O-])=O)C(N)=C([N+]([O-])=O)C(N)([N+]([O-])=O)C1 CMDORWSHEWRPMO-UHFFFAOYSA-N 0.000 description 1
- GDDNTTHUKVNJRA-UHFFFAOYSA-N 3-bromo-3,3-difluoroprop-1-ene Chemical compound FC(F)(Br)C=C GDDNTTHUKVNJRA-UHFFFAOYSA-N 0.000 description 1
- XORHNJQEWQGXCN-UHFFFAOYSA-N 4-nitro-1h-pyrazole Chemical group [O-][N+](=O)C=1C=NNC=1 XORHNJQEWQGXCN-UHFFFAOYSA-N 0.000 description 1
- NVKJOXRVEKMMHS-UHFFFAOYSA-N 5-nitro-1,2,4-triazol-3-one Chemical compound [O-][N+](=O)C1=NC(=O)N=N1 NVKJOXRVEKMMHS-UHFFFAOYSA-N 0.000 description 1
- QJTIRVUEVSKJTK-UHFFFAOYSA-N 5-nitro-1,2-dihydro-1,2,4-triazol-3-one Chemical compound [O-][N+](=O)C1=NC(=O)NN1 QJTIRVUEVSKJTK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- FUHQFAMVYDIUKL-UHFFFAOYSA-N fox-7 Chemical compound NC(N)=C([N+]([O-])=O)[N+]([O-])=O FUHQFAMVYDIUKL-UHFFFAOYSA-N 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- RBLWMQWAHONKNC-UHFFFAOYSA-N hydroxyazanium Chemical compound O[NH3+] RBLWMQWAHONKNC-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical class N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-O nitrosooxidanium Chemical compound [OH2+]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-O 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical class NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 231100000279 safety data Toxicity 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/34—Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0755679A FR2917409B1 (fr) | 2007-06-12 | 2007-06-12 | Derives de dinitropyrazoles, leur preparation et les compositions energetiques les renfermant. |
| FR0755679 | 2007-06-12 | ||
| PCT/IB2008/002535 WO2008152525A2 (en) | 2007-06-12 | 2008-06-06 | Dinitropyrazole derivatives, their preparation, and energetic compositions comprising them. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010530370A JP2010530370A (ja) | 2010-09-09 |
| JP5460584B2 true JP5460584B2 (ja) | 2014-04-02 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010511742A Expired - Fee Related JP5460584B2 (ja) | 2007-06-12 | 2008-06-06 | ジニトロピラゾール誘導体、その製造方法、及び、それを含む活性化合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US8273784B2 (pl) |
| EP (1) | EP2155688B1 (pl) |
| JP (1) | JP5460584B2 (pl) |
| FR (1) | FR2917409B1 (pl) |
| PL (1) | PL2155688T3 (pl) |
| WO (1) | WO2008152525A2 (pl) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2130821B1 (fr) * | 2008-06-06 | 2011-09-21 | Sme | Dérivés du 3,4,5-trinitropyrazole, leur préparation et les compositions énergétiques les renfermant |
| CN102336711A (zh) * | 2011-07-25 | 2012-02-01 | 西安近代化学研究所 | 4-氨基-3,5-二硝基吡唑铅盐及其制备方法和应用 |
| CN104710364B (zh) * | 2015-03-19 | 2020-11-10 | 中北大学 | 3,5-二硝基吡唑-4-硝酸酯及其合成方法 |
| CN104710363B (zh) * | 2015-04-09 | 2017-08-29 | 中国工程物理研究院化工材料研究所 | 含能化合物1‑（2,2,2‑三硝基乙基胺）‑3,5‑二硝基吡唑及其制备方法 |
| FR3085377B1 (fr) | 2018-08-31 | 2020-11-13 | Arianegroup Sas | Procede de preparation de nitropyrazoles |
| CN115124471B (zh) * | 2021-03-24 | 2024-02-13 | 中国工程物理研究院化工材料研究所 | 一类具有高能和低熔点特性的吡唑环类炸药及其合成方法 |
| CN114149372B (zh) * | 2021-11-30 | 2023-06-06 | 湖北航天化学技术研究所 | 一种硝基吡唑含能化合物及其合成方法 |
| FR3130799A1 (fr) | 2021-12-17 | 2023-06-23 | Arianegroup Sas | Procédé de préparation du 3,5-dinitropyrazole |
| CN115043778B (zh) * | 2022-06-27 | 2024-02-13 | 中国工程物理研究院化工材料研究所 | 烷基取代的4-氨基-3,5-二硝基吡唑类低熔点化合物及其制备方法 |
| CN115340506B (zh) * | 2022-08-10 | 2024-08-30 | 北京理工大学 | 一种4-氨基-3-硝氨基噁二唑铜含能化合物及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2624118B1 (fr) | 1987-12-08 | 1990-03-23 | Commissariat Energie Atomique | 4,6-di-(3-amino-5-nitro-1,2,4-triazole)-5-nitropyrimidine, son procede de preparation et materiau explosif la contenant |
| FR2911339B1 (fr) * | 2007-01-16 | 2012-08-03 | Snpe Materiaux Energetiques | Derives du furazane, leur preparation et les compositions energetiques les renfermant |
-
2007
- 2007-06-12 FR FR0755679A patent/FR2917409B1/fr active Active
-
2008
- 2008-06-06 JP JP2010511742A patent/JP5460584B2/ja not_active Expired - Fee Related
- 2008-06-06 WO PCT/IB2008/002535 patent/WO2008152525A2/en active Application Filing
- 2008-06-06 EP EP08807179.0A patent/EP2155688B1/en active Active
- 2008-06-06 PL PL08807179T patent/PL2155688T3/pl unknown
- 2008-12-16 US US12/314,726 patent/US8273784B2/en active Active
-
2012
- 2012-08-27 US US13/595,622 patent/US8440839B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| FR2917409B1 (fr) | 2010-06-04 |
| FR2917409A1 (fr) | 2008-12-19 |
| US8440839B2 (en) | 2013-05-14 |
| PL2155688T3 (pl) | 2016-01-29 |
| WO2008152525A2 (en) | 2008-12-18 |
| JP2010530370A (ja) | 2010-09-09 |
| WO2008152525A3 (en) | 2009-11-12 |
| US8273784B2 (en) | 2012-09-25 |
| US20090186931A1 (en) | 2009-07-23 |
| EP2155688A2 (en) | 2010-02-24 |
| US20120323017A1 (en) | 2012-12-20 |
| EP2155688B1 (en) | 2015-08-05 |
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